


Training Session

by JessiSweet



Category: Supernatural
Genre: F/M, Threesome, losing virginity
Language: English
Status: Completed
Published: 2013-11-03
Updated: 2013-11-03
Packaged: 2017-12-31 10:04:39
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 2,589
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1030396
Author URL: https://archiveofourown.org/users/JessiSweet/pseuds/JessiSweet
Summary: <blockquote class="userstuff">
              <p>You and Dean weren't really friends per say. Mostly just a booty call whenever your schedules collide. So, when he called you up and proposed the challenge of helping deflower his friend, you were more than up for the challenge.</p>
            </blockquote>





	Training Session

The engine of your ‘67 Camaro roared as you drove down the long stretch of dark, abandoned highway. You checked the rearview mirror a few times, not to look behind you but to check your appearance. 

You pulled the car into the small motel parking lot and parked next to a familiar looking Chevy Impala. You killed the engine before grabbing your bag and heading for the motel room door labeled with the crooked number 13. You knocked on the door and immediately hear a gruf, monotone voice call,

“She’s here.”

“I know, Cas. Jeez...” Replied a much more familiar voice. Muted footsteps came close to the door and it opened slowly, revealing your favorite pair of deep emerald eyes. 

“Hi Dean.” You say, smiling. The tension in his shoulders eased and he opened the door to let you in. You stepped inside and saw the owner of the first voice standing in the far off corner of the room.

“So how are you?” Dean asked, closing the door. 

“That’s not why you called me here, is it?” You asked, turning to him, “Because if you wanted to know how I was, you could have taken me to dinner first and then done this.” He smirked at you,

“Always business with you, isn’t it?”

“Well, I’m a very busy girl, Dean.” You began to remove your coat and threw it onto the back of the a chair along with your bag. “So, are we gonna do this or not?” You asked, looking back at the one who you assumed was named Cas. This was definitely a different kind of request and one that you would have normally said no to but, it was Dean after all and he did say please. In fact, he said it about a thousand times. Cas’ eyes were wide and his gaze darted between you and Dean.

“Dean,” he spoke, shifting uneasily, “this is a hot bed of iniquity. I shouldn’t be doing this.”

“Damn it, Cas. Don’t you dare zap your ass out of here. It’s hard enough for me to get in contact with her, twice as hard for us to be in the same town at the same time and damn near impossible for me to be generous enough for me to share her. Now, get over here.” Cas, obviously still uneasy about the whole situation, staggered over, rigid as a board. 

You smiled at him reassuringly. Your hands came up and rested on his shoulders, leaning in close, “Don’t worry,” you spoke, closing the gap between your lips, “this is going to be a very educational experience for you.” You grazed your lips against his and felt Dean stand behind you. You felt Dean’s arms come around you but they don’t wrap around you. Instead, his hands grasp Cas’ wrists and he places Cas’ hands firmly on your hips. 

You shifted so your body was pressed against Cas’, feeling just how rigid he was. You felt dean’s hands move your hair and his lips attach to your neck, suckling marks into the flesh. Cas didn’t move against your lips, just stood awkwardly. You broke the kiss, unintentionally grinding your backside against Dean. 

“What is it?” He asked, chin perched on your shoulder. 

“Dean, I--” Cas began to speak but Dean apparently gathered what was wrong and, not wanting to blow the opportunity, spoke quickly,

“Cas, remember the pizza man?” You quirked your eyebrow at the sudden question.

“Well, yes, of course I do.” Cas responded and you watched Cas start to slowly formulate what Dean was getting at.

“Well, pretend she’s the babysitter.” Dean smirked before kissing your neck again. He walked off to the side to begin disrobing when Cas nodded before locking eyes with you. You didn’t even have a chance to question what all that pizzaman-babysitter talk was about. Cas grabbed you and pulled you close, his one arm wrapped around to your lower back, the other holding your head a slight tilt so your face was pointed up toward him and he kissed you full on the mouth.

You moaned at the sudden intensity and, just as you hands came up to press against his chest, he separated from you. Catching you off guard again, he pushed you onto the bed. You made a small noise of surprise as you bounced on the mattress. Dean looked between you and Cas in concern, his boots now off, his shirt caught on his shoulder as he was trying to pull it off when he saw you get tossed. 

“Easy, Cas.” Dean warned, feeling protective. 

“It’s alright, sweetheart.” You say, sitting up and taking off your shirt. You toss it onto the pile Dean had started. You kicked off your boots and looked up to see Castiel take off his trench coat and tossing it onto the extra chair. When you saw him now, it kind of melted your heart; despite the ravenous look in his eye, he looked small, swimming in the button down shirt where the sleeves were too long, nearly covering his hands. 

He untied his tie and began to undo some of the buttons on his shirt when Dean climbed onto the bed to join you. You smiled as he climbed on top of you, straddling your lap and cupping your face in his hands. He kissed you tenderly and your hands began to roam his thighs, the fly and zipper of his jeans left wide open, revealing the front of his boxers and his hard on. 

Your hands stroked his thighs softly as his tongue began to wrestle with yours. He was a sweetheart to you, always kind, always making sure that when you were together, he was attentive. It was a welcome change from all the other men you had been with. It was always worth the trek for you to come see him. His hands came down, softly groping you through the soft fabric of your bra. He finally backed off, leaving you slightly breathless from the kiss. Dean moved to sit behind you as Cas came onto the bed, grabbing at your legs and opening them, wedging himself between them.

Cas kissed you ravenously, Dean’s hands on your shoulders, your head leaning against his stomach as Cas’ hips started to grind against you, making you moan into his mouth. Dean’s hands came down and unclasped your bra. You let it fall from your shoulders and Dean discarded it onto the growing pile of clothes on the floor. 

Cas made his way off of the bed again, removing his pants, leaving himself in his boxers. He loomed over you for a moment, unbuttoning your jeans and hooking his fingers into the waistband, skillfully pulling them down with your panties, leaving you to be the only one in the room completely exposed. You didn’t have much time to feel self conscious though; Cas sank to his knees on the floor, grabbing your legs and strewing them over his shoulders. 

His mouth attached to your core. He began to lap at the slick wetness, the tip of his tongue flicking at your clit playfully. You were flat on the mattress, trying to stifle in a moan as you felt your legs tense up at the sudden rush of pleasure that began the tight knot in your lower belly. Dean loomed over you, his lips immediately wrapping around your nipple. He nipped at it, releasing the moan you had tried to hide. 

Dean’s hand came up and began to pinch at the neglected nipple as Cas’ tongue darted into you, his hands pressing down on your hips to keep you from bucking up. You arched your back, moaning loud, Dean grabbing hard onto your breast and kneading the flesh in his hand. You were squirming from all the attention, body overwhelmed with pleasure. 

The tightness in your lower belly began to twist and send warming sensations through your body as Cas’ tongue fucked into you and his thumb rubbed circles into your clit. You moaned loud, fingers burying into Cas’ hair.

“Oh fuck, Cas! I’m gonna come!” Your hips, despite him holding you down, bucked up, grinding into his face as the tightness in your belly unwound and spread through you, shudders and gasping moans escaping your mouth. Cas let your legs down as he sat back on his haunches, Dean following suit, a smirk on his face. 

“Way to go, Cas.” Dean spoke, climbing off of the bed and ridding himself of his jeans and boxers. Cas looked unsure of himself suddenly, as if he didn’t know where to go from that point on. 

“Do I keep going?” He asked. You were panting but propped yourself up on your elbows, wanting to give Cas some encouragement, 

“Please fuck me, Cas.” You saw a blush creep onto his face as he climbed up to his feet. He removed his boxers and climbed up onto the bed. You shifted so you were more in the middle and Dean came back up behind you. Cas looked to Dean for guidance as to where he should go next. 

You smiled at him reassuringly, settling him so was resting on his knees. 

“Just hold onto my hips.” You say as you slowly straddle his lap, letting the tip of his cock rubbing against your slick folds. He made a guttural sound as the sudden pleasure shuddered through him. His hands clasped onto your hips as you lined him up at your entrance, slowly sinking down onto his lap. He let out a deep throat groan as you settled to his size. Your hands rested onto his shoulders as you began to very slowly ride him. “Does that feel good?” You ask him, innocently, looking right into his bright blue orbs that were half lidded with lust. 

“Yes. Very much so.” His rasping voice came out to you. You heard the sounds of a cap opening and then closing and peeked over your shoulder to see Dean prepping his own hard cock. You turned your focus back to Cas, a flutter raging into your belly from knowing what was going to happen next. 

Dean came up close behind you, his hand pressing softly against your back pressing your chest into Cas’ as he lined himself up with your back entrance. You made a soft sound as he pressed against your tight hole. 

“I’m not gonna hurt you. I promise.” Dean said, his hand coming down to Cas’ fingers over the angels, the other on his cock as he eased you down slowly onto his cock. You let out a long moan capped off with a hiss. “Does it hurt? Do you want me to stop?” Dean asked. You eased your body, letting yourself get used to the new feeling, letting the tension in your muscles dissipate.

“No. It’s okay.” You said finally. 

“You sure?” He asked again. Instead of verbally responding, you slowly brought your body up, before lowering it back down on both of their cocks. All three of you let out soft relieved moans as you landed back into their laps. 

Slowly you began to ride them. Normally, you would be able to have a fast pace and keep up with it but now with Dean in such a tight, tender spot, it was hard for you to get going comfortably. Dean shifted slightly, his cock burying deeper into you, causing you to cry out. 

“I’m sorry!” He said, hands dashing up to your sides. 

“It’s okay. I-it....it felt good.” You smiled. Your pace quickened, your body starting to not only relax to the feeling but really starting to enjoy it. You kept letting out shallow pants the heat from the pair of them stifling as Dean breathed hard on you back and Cas down your throat. You bit your lip hard as you set the pace of lowering yourself onto Cas then rocking back onto Dean, filling you completely before coming up and starting all over again. 

Your legs began to burn and your stomach began to tighten up but you were getting too tired to carry on. 

“D-dean.” You spoke, your voice hoarse from your throat being dry. Dean knows that sound in your voice; desperation, wanting to continue but needing his help. He quickly wraps his arms around your waist, moving himself up a bit on his legs, pressing into you more and making you moan loud as lifted you up a bit. Cas’ face was slumped down, his breath hot against your breasts, his nails digging into your thighs as Dean’s face fell to the crook of your neck. 

You swallowed hard before Dean started to thrust into you, it was a moderate speed, gentle even. Cas took a note from Dean and shifted himself so he was able to thrust up into you. You were letting out a slew of expletives when their pace quickened. 

Dean’s arms were holding you close to him, his hot breath and moans beating out against your shoulder almost as quick as his thrusts into you. Cas, not to be outdone was fucking up into, fingers now on your ass, scratching and pulling to give Dean better access to your ass. You pressed on Cas’ shoulders, nails digging into his soft flesh, head tilted back, resting on Dean’s shoulder.

All the touching and closeness was a lot to take; you were nearing another climax even before one of Dean’s hands went rogue and ventured down your belly to your wet mound that Cas was still mercilessly pounding into. His finger settled on the still too sensitive bundle of nerves which made your hips buck. Your movement only made Dean pull you impossibly closer, his middle finger rubbing down hard against your clit. You were panting, your voice an uncontrollably higher octave from sheer pleasure as you closed your eyes tight, fingers digging angry red half moon shapes into Cas’ shoulders as you cried your release up to the ceiling.

Cas came first his thrusts slowing his legs feeling like they had been filled with cement from the vigorous movements which gave Dean a chance to pull you back, settling you completely into his lap and fucking up into you. Your soft cries and the sound of your blissed out voice calling his name was what did it in for him, his own personal pleasure spilling into you. 

You three collapsed onto the motel room bed, a mess of tangled limbs. It wasn’t like you to stick around and cuddle but Dean was always that exception to any rule. You didn’t know what the morning was going to be like, whether there was going to be any kind of awkward, “I’ll call you again sometime” chat with Dean or what Cas would say, if anything. What mattered most was not all the work you knew you had to do tomorrow, how it was a travel day for you and that you really were supposed to hit the road early in order to make it to the meeting 2 states over, or the fact that you had dodged another string of calls from your mother who surely wanted to nag you for dumping your fiancee the day prior. What mattered now was Dean’s arms wrapped around your middle and Cas’ face close to your chest, his own hands on your hips and both of their breaths coming to a collective deep slow rhythm as they fell asleep and how, just for this one night, you were their entire world.


End file.
